Azo dye and process of making same.



UNITED STATES PATENT OFFICE.

PAUL JULIUS AX D ERNST FUSSENEGGER, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, ASSIGNORS'TQ BADISUHE ANILIX & SODA FABRIK, OF LUDWTGSHAFEN-ON-THE-RHINE,

G RMANY, A CORPORATION.

AZO DYE AND PRocEss 0F MAKI NGr SAM Ei T 0 all whom it mag/concern:

Be iteknown that we, PAUL JULIUS and Ernst F i'ssENEooER, doctors of philosophy and chemists, subjects of, the Emperor of Austria-Hungary, residing at Ludwigshafenon-the-Rhine,Germany, have invented new and useful Improvements in Azo Dyes and Processes of Making the Same, of which the following isa specification.

In the specification of British Letters Patent No. 25,977 A D. 1906 is described the production of green coloring matters of the triphenylmethanie series by combining an alkylated dMni'fdo-benzhydrol with 2.6 dinitro diphenyl {amin 4.3- disulfonic acid, or with 2.4-dinitro-diphenyl-amin-6.3 disulfonic acid, or with a derivative of these acids, in which the second para position to the imido group isi'only occupied by hydrogen, and then oxidizing the leuco compounds so obtained. j v

If the aforementioned leuco compounds (which are hereinafterilieferred to as dinitro compounds of triphenyl-methane derivatives) be treated with a reducing agent, the two nitro groups. can be converted into amido groups, the corresponding diamido compounds of triphenyl-methane derivatives being obtained, the simplest representatives of these compounds having respectively the following formulae;

We have further discovered that these diamido compounds of triphenyl-methane derivatives can be combined with diazo compounds yielding azo coloring matters. .The diazo compounds which can be used accord ing to our invention may be eithenof the benzene, or of the naphthalene, series and may contain a sulfonic acid, .or a carboxy lic acid, or a hydroxyl group, or be otherwlse substituted, or not. The azo coloring matters obtained according to our invention are Specification of Letters Patent. l I 7' Application filed October a. 1907. Serial NOB-396.761

, grees centigrade.

atented Feb. 1 1, 1908.

The coloring matter which we desire to beunderstood as claiming specifically is that obtainable: by combining diazotized 2.5-dichloranilin with diamido-phenylamido-tetramethyl diamido triphenyl methane -'disulionic acid. It consists of a yellow powder yielding a yellowish brown solution in water and dyeing wool yellow, which shade becomes green upon treatment with bichromate. Upon a reduction with tin and hydrochloric acid it is split up in the normal 'manner for azo dyes.

The reduction of the dinitro compounds of triphenyl-methane derivatives intothe corresponding diamido compounds can be effected, for instance, by means of iron filings in aqueous solution, or suspension, according to the following directions. five hundred 500)parts of iron filings and two thousand (2,000) parts of water and add, gradually, during aperiod of two (2) hours, six hundredand seventy-one (671) parts of the leuco compound obtainable by condensing tetra methyl diamido benzhydrol with Z.6-(liIlitIO-(liPllGIlYl-MlliIl-4.3-d.l sulfonic acid, whereupon the temperature rises spontaneously to about seventy-five (75) de- Stir the whole, while maintaining this temperature, until the reduction iscomplete, which is the casein about from six (6), to ten, (10), hours. Then add one hundred and thirty (130) parts of sodium carbonate and boil until the iron is precipitated, filter this off, add dilute sulfuric acid to the filtrate (if necessary after concentrating the said filtrate by evaporation) until it is just acid to Congo paper, and

filter off the-diamido compound.

The following examples will serve to illustrate further the nature of this invention and how it can be carried into practical effect, but

our invention is not confined to these examples. The parts are by weight.

ring, into a solution of sixty-one and onesoluble water and dye unniordanted wool from yellow tobrown shades, which'arecon verted into from blue to yellowish green Stir together Example '1. l 'iazotize sixteen and one tenth (6 1.1) parts of the reduced leuco com-' pound prepared from tetra-methyl-diamidoenzhydrol and 2.-6dinitro-diphen l-amin- 4.3d1sulfonic acid, in .about our undred I (400) parts of water to which sufficient sodium carbonate has been added to maintain the whole alkaline. The coloring mfitter ter separates out as'a yellow precipitate.

,about half an hour (30 minutes), heat to a temperature of fifty (50) degrees centigrade and filter off and press and dry the coloring powder matter which'consists of a yellow easily soluble water yielding a y lowish brown solution which dyes wool yellowish with bi'chromate, become been added to maintain the whole alkaline.

Stir for half an hour (30 minutes), then heat to a temperature of from fifty to siirty degrees centigrade, Precipitate the coloring matter by means of common salt, and filter it off and press and dry it. The coloring matter consists of a brownish red powder which yields a yellowish brown solution in water, and dyes. wool brown shades which, upon treatment with a bichromate, are converted into blue-green. It is soluble one-tenth (61.1) parts of the in concentrated sulfuric acid yielding a violet solution.

. Now What weclaim 1. The process of producing azo coloring matter by combining a hereinbefore defined diazo compound with diamido-phenyl-amido tetra alkyl diamido triphenyl -methane-' disulfonic acid.

2. The process, of producing'azo coloringmatter by combining diazotized 2.5-dichloranilin with diamido-phenyl-amido-tetra-' methyl diamido triphenyl-methanedisulfonic acid.

'3. As new articles of manufacturethe azo coloring matters which can be obtained by combining a hereinbefore defined diazo compound with diamido-phenyl-amido tetra-alyl diamido triphenyl methane disulfonic matters are soluble in 50 tween yellow and brown which is changed into blue and yellowish green acid, which coloring water and dye unmordanted wool a shadebea shade between upon treating the material with bichromatel- 4:. As a new article of manufacture the azo. coloring matter which can be obtained by combining diazotized 2.5-dichlor-anilin with diamidophenyl amido tetra methyl iii-- amido triphenyl methane disulfonic acid, which coloringlmatterlis soluble'in'water and dyes unmordanted wool yellow, which shade into green upon treating the material with bichromate.

is changed In testimony whereofwe have hereunto set our hands in the presence of two subscribing witnesses. I

PAUL JULIUS.

ERNST. FUSSENEGGER. Witnesses:

ERNEST F. EHRHiA- RDT,

J. Arno. LLOYD. 

